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CAS No. : | 14389-86-7 | MDL No. : | MFCD00051940 |
Formula : | C14H12O3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | GMOYUTKNPLBTMT-UHFFFAOYSA-N |
M.W : | 228.24 | Pubchem ID : | 1810581 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Carbonyldiimidazole (CDI) (5.10 g, 31.5 mmol) was dissolved in 50 ml dry THF with stirring at room temperature under an argon atmosphere, and 2-(benzyloxy)benzoic acid (compound 2.4) (7.18 g, 31.5 mmol) was added to the mixture. After the evolution of CO2 ceased (ca. 5 min) the reaction mixture was stirred for an additional 10 minutes and <strong>[17672-21-8]methyl 2-amino-3-hydroxybenzoate</strong> (3.5 g, 21 mmol) was added. After stirring for an additional 10 minutes at room temperature, the reaction mixture was heated under reflux for 18 hours. The reaction mixture, brown in color, was concentrated and dissolved in a minimum volume of ethyl acetate (EtOAc). Silica gel (60-100 mesh) was added to make a slurry and solvent was evaporated to dryness. Column chromatography was performed using 20% EtOAc in hexane to give a light yellow solid (6.9 g, 87%): mp 104-105 C.; Rf 0.328 (20% EtOAc in hexanes); 1H NMR delta 3.80 (s, 3H), 5.50 (s, 2H), 7.05 (d, 1H, J=8.1 Hz), 7.10 (t, 1H), 7.24 (m, 2H), 7.34 (m, 3H), 7.47 (m, 3H), 7.61 (d, 1H, J=7.8 Hz), 8.27 (d, 1H, J=9.0 Hz), 9.28 (brs, 1H, NH), 12.27 (s, 1H, OH); 13C NMR delta 52.20, 70.80, 113.34, 120.94, 121.27, 121.58, 122.97, 125.70, 126.05, 126.93, 128.01, 128.21, 128.60, 132.69, 133.93, 136.22, 150.76, 157.01, 165.51, 167.57; CIMS m/z 378 (MH+); HRMS m/z calc'd for C22H20NO5: 378.1341, found 378.1343. |